GB1308106A - Phenoxyhydroxypropylamines and their preparation - Google Patents

Phenoxyhydroxypropylamines and their preparation

Info

Publication number
GB1308106A
GB1308106A GB2199471A GB2199471A GB1308106A GB 1308106 A GB1308106 A GB 1308106A GB 2199471 A GB2199471 A GB 2199471A GB 2199471 A GB2199471 A GB 2199471A GB 1308106 A GB1308106 A GB 1308106A
Authority
GB
United Kingdom
Prior art keywords
compound
hydrolysing
prepared
methoxyethyl
reacting
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2199471A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hassle AB
Original Assignee
Hassle AB
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=20259298&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=GB1308106(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Hassle AB filed Critical Hassle AB
Publication of GB1308106A publication Critical patent/GB1308106A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
    • C07C317/10—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1308106 Substituted phenoxy-hydroxy propylamines HASSLE AB 19 April 1971 [18 Feb 1970] 21994/71 Heading C2C Novel compounds of the Formula IV wherein R<SP>1</SP> is isopropyl or t-butyl, A is a straight or branched C 1-4 alkylene chain and Z is -OR<SP>2</SP>, -SO 2 R<SP>2</SP>, -SOR<SP>2</SP>, -SR<SP>2</SP>, NR 3 -COR<SP>2</SP>, NR 3 SO 2 R<SP>2</SP> or NR<SP>3</SP>COOR<SP>2</SP> wherein R<SP>2</SP> is straight or branched C 1-3 alkyl and R<SP>3</SP> is hydrogen or a straight or branched alkyl radioal and pharmaceutically acceptable acid addition salts thereof may be prepared by (i) reacting a compound V wherein X is an unsubstituted ethylene oxide ring or -CHOHCH 2 -halogen with a compound R<SP>1</SP>NHCONHR<SP>1</SP> or R<SP>1</SP>NH 2 ; (ii) reductively alkylating IV wherein R<SP>1</SP> is H with acetone to produce IV, R<SP>1</SP> = iPr; (iii) alkylating IV R<SP>1</SP> = H with Hal-CH(CH 3 ) 2 where Hal is a halogen atom; (iv) hydrolysing a compound wherein R<SP>4</SP> is a hydrolytioally removable group; (v) hydrolysing a compound with strong acid or strong alkali (vi) hydrolysing or pyrolysing a compound wherein R<SP>6</SP> and R<SP>6</SP> are hydrogen, C 1-4 alkyl, aralkyl or aryl; (vii) hydrolysing or hydrogenolysing a compound wherein R<SP>7</SP> is an amine protecting group; (viii) reacting XCH 2 NHR<SP>1</SP> or XCH 2 NR<SP>1</SP>R<SP>7</SP> with a phenolate (ix) reducing a compound wherein B is -CHOHCO- or -COOH 2 -, (x) hydrolysing a compound wherein R<SP>8</SP> is C 1-4 alkyl, aralkyl or aryl or, (xi) hydrogenolysing a compound wherein Y means the benzene ring is substituted with 1 to 4 halogen atoms. The intermediates V may be prepared by reacting an appropriately para-substituted phenol with chlorohydrin followed in the case where X is CHOHCH 2 Cl, by treatment with hydrochloric acid. 2 - Hydroxy - 3 - [p - (methoxyethyl) - phenoxy]- N - isopropyl propionamide may be prepared by reacting the free acid with isopropylamine, the free acid in turn being prepared by condensingp-methoxy ethyl phenol with 2-hydroxy- 3-chloropropionic acid. A 1 - isopropylamino - 3 - [bromo - p - (#- methoxyethyl) - phenoxy] - propanol - 2 may be prepared by brominating p-(#-methoxyethyl)- phenyl to give a brcmo-p-(#-methoxyethyl)- phenol which is reacted with chlorohydrin followed by isopropylamine to yield the required compound. Pharmaceutical compositions of the compounds IV may be used for treatment of heart diseases and vascular diseases when administered orally, parenterally or rectally with excipients or diluents.
GB2199471A 1970-02-18 1971-04-19 Phenoxyhydroxypropylamines and their preparation Expired GB1308106A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE02050/70A SE354851B (en) 1970-02-18 1970-02-18

Publications (1)

Publication Number Publication Date
GB1308106A true GB1308106A (en) 1973-02-28

Family

ID=20259298

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2199471A Expired GB1308106A (en) 1970-02-18 1971-04-19 Phenoxyhydroxypropylamines and their preparation

Country Status (17)

Country Link
US (4) US3873600A (en)
JP (2) JPS5317587B1 (en)
AT (3) AT317181B (en)
BE (1) BE762629A (en)
CA (1) CA982140A (en)
CH (8) CH572896A5 (en)
DE (1) DE2106209C3 (en)
DK (1) DK129446B (en)
FI (1) FI55024C (en)
FR (1) FR2081523B1 (en)
GB (1) GB1308106A (en)
IE (1) IE35106B1 (en)
MY (1) MY7500161A (en)
NL (1) NL160549C (en)
NO (1) NO132798C (en)
SE (1) SE354851B (en)
ZA (1) ZA71682B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0041295A1 (en) * 1980-05-26 1981-12-09 Aktiebolaget Hässle Process for the preparation of 1-isopropylamino-3-(4-(2-methoxy-ethyl)-phenoxy)-2-propanol
EP0041760A1 (en) * 1980-06-04 1981-12-16 Aktiebolaget Hässle Process for the preparation of 1-isopropylamino-3-(4-(2-methoxy-ethyl)-phenoxy)-2-propanol
US8338489B2 (en) 2007-10-19 2012-12-25 Université Victor Segalen—Bordeaux 2 Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas
US8987262B2 (en) 2007-10-19 2015-03-24 Universite de Bordeaux Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE384853B (en) * 1972-04-04 1976-05-24 Haessle Ab PROCEDURE FOR THE PREPARATION OF NEW AMINES
US4145442A (en) * 1972-04-04 1979-03-20 Aktiebolaget Hassle Phenoxy-hydroxypropylamines, their preparation, and method and pharmaceutical preparations for treating cardiovascular diseases
US4035420A (en) * 1972-07-06 1977-07-12 Aktiebolaget Hassle Substituted ureido alkylene phenoxy propanolamines
US4041075A (en) * 1973-12-12 1977-08-09 Imperial Chemical Industries Limited Phenoxy-alkanolamine derivatives
AT334385B (en) * 1973-12-20 1976-01-10 Chemie Linz Ag PROCESS FOR THE PREPARATION OF NEW PHENOXYPROPYLAMINE DERIVATIVES AND THEIR SALTS
SE7402096L (en) * 1974-02-18 1975-08-19 United Aircraft Corp
US4145363A (en) * 1975-02-05 1979-03-20 Yamanouchi Pharmaceutical Co., Ltd. 4-Carbamoylamino-α-aminomethylbenzyl alcohol derivatives
FR2330383A1 (en) * 1975-11-06 1977-06-03 Synthelabo NEW PHENOL SUBSTITUTE ETHERS, THEIR SALTS, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM
DE2645710C2 (en) * 1976-10-09 1985-06-27 Merck Patent Gmbh, 6100 Darmstadt Phenoxy-aminopropanols, process for their manufacture and pharmaceutical preparation
IT1109002B (en) * 1977-09-22 1985-12-16 Menarini Sas DERIVATIVES OF 2 OXAZOLIDONE AND THEIR PREPARATION METHODS
US4243681A (en) * 1977-10-11 1981-01-06 Mead Johnson & Company Alkylthiophenoxypropanolamines and pharmaceutical compositions and uses thereof
US4341718A (en) * 1978-07-03 1982-07-27 American Home Products Corporation α-[(Alkylamino)-methyl]-β-aryloxy-benzeneethanols exhibiting antiarrhythmic activity
US4329502A (en) * 1978-08-28 1982-05-11 Syva Company Propranolol antigen conjugates and antibodies
FR2477537A1 (en) * 1980-03-07 1981-09-11 Francaise Sucrerie NOVEL ACYLATED GUANIDINES, UREAS AND SUBSTITUTED UREAS, THEIR MANUFACTURING PROCESS AND THEIR APPLICATION AS MEDICAMENTS
SE8004087L (en) * 1980-06-02 1981-12-03 Haessle Ab NEW PARA-SUBSTITUTED 3-PHENOXY-1-ALKYLAMINOPROPANOL-2 WITH BETARETTY RECEPTOR BLOCKING PROPERTIES, AND PROCEDURES FOR THEIR PREPARATION, PHARMACEUTICAL PREPARATIONS CONTAINING THE SAME, AND METHOD OF ACCOUNTING ...
SE8004088L (en) * 1980-06-02 1981-12-03 Haessle Ab NEW SUBSTITUTED 3-PHENOXI-L-ALCOXICARBONYLALKYLAMINO-PROPANOL-2 WITH BETA-RECEPTOR BLOCKING PROPERTIES AND PROCEDURE FOR THEIR PREPARATION, PHARMACEUTICAL PREPARATIONS OF THE METHOD
US4342783A (en) * 1980-06-30 1982-08-03 Synthelabo Anti-glaucoma agent
FR2497194B1 (en) * 1980-08-07 1985-06-14 Sandoz Sa NEW PHENOLIC COMPOUNDS
CH643527A5 (en) * 1980-10-24 1984-06-15 Ciba Geigy Ag Process for the preparation of 1-alkylamino-3-(4-(2-lower alkoxy-ethyl)phenoxy)-2-propanols
DE3151201A1 (en) * 1981-12-23 1983-07-28 Beiersdorf Ag, 2000 Hamburg SUBSTITUTED PHENOXYALKANOLAMINE AND PHENOXYALKANOL-CYCLOALKYLAMINE, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICAL PREPARATIONS CONTAINING THESE COMPOUNDS AND INTERMEDIATE PRODUCTS
US4450172A (en) * 1982-03-10 1984-05-22 E. I. Du Pont De Nemours And Company Antihypertensive polyhalohydroxyisopropyl phenylalka(e)noic acid esters of alkylaminohydroxypropyloxyphenylalkyl alcohols
DE3210061A1 (en) * 1982-03-19 1983-09-22 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING PROPAFENONE
SE457505B (en) * 1984-01-10 1989-01-09 Lejus Medical Ab LAMINATED ORAL PHARMACEUTICAL COMPOSITION AND PROCEDURES FOR ITS PREPARATION
US5081154A (en) * 1984-01-10 1992-01-14 Aktiebolaget Hassle Metoprolol succinate
FR2568249B1 (en) * 1984-07-25 1986-12-05 Lipha AMINO-1 ARYLOXY-3 PROPANOLS-2, PREPARATION METHODS AND MEDICINAL PRODUCTS CONTAINING THEM
GB8519154D0 (en) * 1985-07-30 1985-09-04 Ici Plc Aromatic ethers
US4866040A (en) * 1986-01-06 1989-09-12 Alfred Stracher Aminocarnitine directed pharmaceutical agents
US5008288A (en) * 1986-01-06 1991-04-16 Alfred Stracher Carnitine directed pharmaceutical agents
WO1988000190A1 (en) * 1986-06-25 1988-01-14 Massachusetts Institute Of Technology Optically active derivatives of glycidol
JPS6388944U (en) * 1986-12-01 1988-06-09
JPS6445265A (en) * 1987-08-06 1989-02-17 Kotobukiya Goushi Lidded box having socket and spigot part and its manufacture
ES2011584A6 (en) * 1989-05-26 1990-01-16 Esteve Quimica Sa Industrial process for obtaining an aryloxypropanolamine
GB8925032D0 (en) * 1989-11-06 1989-12-28 Ici Plc Chemical compounds
US5107034A (en) * 1990-03-28 1992-04-21 Hoechst Celanese Corporation Method for producing 4-(2'-methoxyethyl)phenol
ES2065291B1 (en) * 1993-07-30 1995-10-01 Prodesfarma Sa "1-ARYLOXI-3-ALKYLAMINO-2-PROPANOLS NITRATE ESTERS, USE AND CORRESPONDING PHARMACEUTICAL COMPOSITION"
US5859390A (en) * 1996-10-23 1999-01-12 Hill-Rom, Inc. Hospital bed scale mounting apparatus
US5998458A (en) * 1997-06-25 1999-12-07 University Technology Corporation Method of treating heart failure
KR100489649B1 (en) * 1998-04-14 2005-09-02 삼성정밀화학 주식회사 (S) -3-substituted-2-hydroxypropylamine preparation method
KR100469947B1 (en) * 1998-04-14 2005-04-08 삼성정밀화학 주식회사 Manufacturing method of chiral (S) -3-amino-1,2-propanediol
KR100469946B1 (en) * 1998-04-14 2005-05-17 삼성정밀화학 주식회사 Manufacturing method of chiral (S) -2,3-substituted-1-propylamine derivative
US6924441B1 (en) 1999-09-29 2005-08-02 Hill-Rom Services, Inc. Load cell apparatus
SE0100824D0 (en) * 2001-03-09 2001-03-09 Astrazeneca Ab Method III to obtain microparticles
BR0313593A (en) 2002-08-19 2005-07-12 Pfizer Prod Inc Combination therapy for hyperproliferative diseases
AP2501A (en) 2003-05-30 2012-10-22 Ranbaxy Lab Ltd Substituted pyrrole derivatives
US20050037063A1 (en) * 2003-07-21 2005-02-17 Bolton Anthony E. Combined therapies
US7176391B2 (en) * 2004-09-13 2007-02-13 Hill-Rom Services, Inc. Load cell to frame interface for hospital bed
KR20080016527A (en) * 2005-01-31 2008-02-21 밀란 래보러토리즈, 인크. Pharmaceutical composition comprising hydroxylated nebivolol
GT200600381A (en) 2005-08-25 2007-03-28 ORGANIC COMPOUNDS
US7741317B2 (en) 2005-10-21 2010-06-22 Bristol-Myers Squibb Company LXR modulators
JP2009514851A (en) 2005-11-08 2009-04-09 ランバクシー ラボラトリーズ リミテッド (3R, 5R) -7- [2- (4-Fluorophenyl) -5-isopropyl-3-phenyl-4-[(4-hydroxymethylphenylamino) carbonyl] -pyrrol-1-yl] -3,5 -Preparation of dihydroxy-heptanoic acid hemi-calcium salt
US7888376B2 (en) 2005-11-23 2011-02-15 Bristol-Myers Squibb Company Heterocyclic CETP inhibitors
WO2008070496A2 (en) 2006-12-01 2008-06-12 Bristol-Myers Squibb Company N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases
US9782488B2 (en) * 2007-03-12 2017-10-10 Nektar Therapeutics Oligomer-beta blocker conjugates
CN102381995B (en) * 2010-08-31 2015-04-15 扬子江药业集团北京海燕药业有限公司 Preparation method of metoprolol
CN102295569B (en) * 2011-07-04 2014-05-21 南京工业大学 Method for preparing (S)-metoprolol succinate
RU2618628C1 (en) 2013-04-17 2017-05-05 Пфайзер Инк. N-piperidin-3-yl-benzamide derivatives for cardiovascular diseases treatment
WO2016055901A1 (en) 2014-10-08 2016-04-14 Pfizer Inc. Substituted amide compounds
SG11202107614PA (en) 2019-01-18 2021-08-30 Astrazeneca Ab Pcsk9 inhibitors and methods of use thereof
CN112645827A (en) * 2020-12-25 2021-04-13 浙江普洛家园药业有限公司 Method for continuously synthesizing metoprolol and salt thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1220440B (en) * 1962-02-14 1966-07-07 Sanol Arznei Schwarz Gmbh Process for the preparation of derivatives of 1- (o-bromophenoxy) -2-hydroxy-3-aminopropane and their acid addition salts
GB1199037A (en) * 1967-09-27 1970-07-15 Ici Ltd Alkanolamine Derivatives
US3466325A (en) * 1965-04-30 1969-09-09 Haessle Ab 1-(ortho-alkenyl phenoxy) - 2-hydroxy-3-isopropylaminopropanes and the salts thereof
US3637827A (en) * 1966-01-06 1972-01-25 Smith Kline French Lab Benzhydryloxy-cyclopropanecarboxylic acids and amides
US3541130A (en) * 1967-02-06 1970-11-17 Boehringer Sohn Ingelheim 1-(cyanophenoxy)-2-hydroxy-3-tert.-butylamine propanes
DE1937477C3 (en) * 1969-07-23 1980-04-10 C.H. Boehringer Sohn, 6507 Ingelheim I-phenoxy-2-hydroxy-3- (l -methylcycloalkylamino) propane, process for their preparation and medicaments containing them
JPS5247447A (en) * 1975-09-29 1977-04-15 Touhoku Nougiyou Shikenjiyouch Blue film utilizing method for growing of paddy rice young plant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0041295A1 (en) * 1980-05-26 1981-12-09 Aktiebolaget Hässle Process for the preparation of 1-isopropylamino-3-(4-(2-methoxy-ethyl)-phenoxy)-2-propanol
EP0041760A1 (en) * 1980-06-04 1981-12-16 Aktiebolaget Hässle Process for the preparation of 1-isopropylamino-3-(4-(2-methoxy-ethyl)-phenoxy)-2-propanol
US8338489B2 (en) 2007-10-19 2012-12-25 Université Victor Segalen—Bordeaux 2 Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas
US8987262B2 (en) 2007-10-19 2015-03-24 Universite de Bordeaux Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas
US9173858B2 (en) 2007-10-19 2015-11-03 Universite de Bordeaux Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas

Also Published As

Publication number Publication date
JPS5317587B1 (en) 1978-06-09
BE762629A (en) 1971-08-09
JPS5755710B2 (en) 1982-11-25
DK129446B (en) 1974-10-14
ZA71682B (en) 1971-10-27
FI55024B (en) 1979-01-31
US3873600A (en) 1975-03-25
DE2106209B2 (en) 1979-08-30
CH563340A5 (en) 1975-06-30
JPS53101322A (en) 1978-09-04
CH576938A5 (en) 1976-06-30
CH572897A5 (en) 1976-02-27
DE2106209A1 (en) 1971-08-26
FR2081523A1 (en) 1971-12-03
AT310144B (en) 1973-09-25
NO132798B (en) 1975-09-29
FR2081523B1 (en) 1974-08-02
US3928601A (en) 1975-12-23
AT307386B (en) 1973-05-25
CH572895A5 (en) 1976-02-27
SE354851B (en) 1973-03-26
CH563339A5 (en) 1975-06-30
CH572896A5 (en) 1976-02-27
NL7101885A (en) 1971-08-20
IE35106L (en) 1971-08-18
NL160549C (en) 1979-11-15
CH578507A5 (en) 1976-08-13
CH563338A5 (en) 1975-06-30
DK129446C (en) 1975-03-03
FI55024C (en) 1979-05-10
NL160549B (en) 1979-06-15
CA982140A (en) 1976-01-20
MY7500161A (en) 1975-12-31
AT317181B (en) 1974-08-12
NO132798C (en) 1976-01-07
IE35106B1 (en) 1975-11-12
US3876802A (en) 1975-04-08
DE2106209C3 (en) 1980-05-29
US3998790A (en) 1976-12-21

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746D Case decided by the comptroller (sect. 46(3)/1977)
746A Appeal to the patents court (sect. 46/1977)
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746D Case decided by the comptroller (sect. 46(3)/1977)
746B Proceeding under section 46(3) patents act 1977
746D Case decided by the comptroller (sect. 46(3)/1977)
746D Case decided by the comptroller (sect. 46(3)/1977)
746D Case decided by the comptroller (sect. 46(3)/1977)
746D Case decided by the comptroller (sect. 46(3)/1977)
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746D Case decided by the comptroller (sect. 46(3)/1977)
746D Case decided by the comptroller (sect. 46(3)/1977)
746B Proceeding under section 46(3) patents act 1977
746D Case decided by the comptroller (sect. 46(3)/1977)
746B Proceeding under section 46(3) patents act 1977
PE20 Patent expired after termination of 20 years